Ethanol → HCID 178451916, compound

HRID 1470947Notes

Reaction equation

HRID 1470947 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19](B4OC(C)(C)C(C)(C)O4)=[CH:18][CH:17]=3)[CH2:14][CH2:13][CH:12]2[C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:41]1[N:42]=[C:43]([C@@H:46]2[CH2:50][CH2:49][CH2:48][N:47]2[C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[NH:44][CH:45]=1.C(O)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH:12]([C:31]3[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=3)[CH2:13][CH2:14][CH:15]2[C:16]2[CH:21]=[CH:20][C:19]([C:45]3[N:44]=[C:43]([C@@H:46]4[CH2:50][CH2:49][CH2:48][N:47]4[C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[NH:42][CH:41]=3)=[CH:18][CH:17]=2)=[CH:9][CH:10]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 56605192tert-Butyl (2S)-2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylateHCID 672365801-(4-Tert-butylphenyl)-2-(4-nitrophenyl)-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidine

Product 1

HCID 178451916HCID 178451916, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Procedure

The product from Example 40B (0.7 g, 1.33 mmol), (S)-tert-butyl 2-(4-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (0.462 g, 1.463 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.109 g, 0.133 mmol) in a mixture of toluene (6 mL), ethanol (6 mL) and a 1N aq. sodium bicarbonate solution (1.6 mL, 1.6 mmol) was reacted according to the procedure in Example 39F to provide the title compound (0.66 g, 78%, yellow solid) as a mixture of stereoisomers.

Sources & evidence

ORD record
ord-b7587e593af34e38a385da7fe7726773
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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